HCID 66888570, compound → HCID 49854432, compound

HRID 1895556Notes

Reaction equation

HRID 1895556 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1([CH3:34])[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][N:15]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=O>C(O)(=O)C>[C:8]([C:7]1[C:2]2[N:1]=[C:12]([C:14]3([CH3:34])[CH2:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][N:15]3[C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[NH:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)(=[O:10])[NH2:9]

Participants

3

Reactant 1

HCID 66888570HCID 66888570, compound

Product 1

HCID 49854432HCID 49854432, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

Step-5: A solution of benzyl 3-((2-amino-3-carbamoylphenyl)carbamoyl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (40 mg, 0.087 mmol) in acetic acid (2 ml) was heated to 80° C. and stirred overnight. The reaction was further heated to 120° C. for 3 h. The reaction mixture was concentrated, neutralized with aq. NaHCO3 and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and evaporated. Purification of the crude product by preparative TLC using hexane/ethyl acetate (1:1) mixture as eluent afforded benzyl 3-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate. MS (ES+): m/z 441.22 [M+H]+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customPurification of the crude product by preparative TLC

Sources & evidence

ORD record
ord-c5a9c6c47317470ba9b1213761d12adf
Source dataset
uspto-grants-2013_08
Patent number
US08513433B2

Reaction notes

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